Sulphuric esters of halogenated fatty acids



Patented June 6, 1933 1 vireo STATES PATENT OFFICE WALTER, T..WINCKLER, CI-IICAGO, ILLINOIS, .ASSIGNOR T VON WINKLEB LABO- RATORIES, INCORPORATED, OF CHICAGO, ILLINOIS, A CORPORATION OF ILLINOIS I No Drawing.

sunrnunro nsrnns or- HALOGENATED' FATTY ACIDS This invention relates to an improved pharmaceutical composition of substantially the same general type as that disclosed 1n my copending applications bearing Serial Nos. 245,051 and 269,880, filed January 6,

i 1928 and April 13, 1928 respectively.

This improved pharmaceutical compound has similar medical properties and is compounded of substantially the same ingredicuts as those disclosed in my copending application bearing Serial No. 245,051, but the ingredients are compounded in an entlrely different sequence and manner and the resulting compound has an entirely different organic structure and different properties which are better suited for the purposes herein set forth; l

The main objects of my invention are to provide an improved method of making a pharmaceutical compound for avoldlng decomposition and disassociation thereof very dilute solutions; to provide a composition that is soluble in water; to provide a composition of improved stability which is capable of retaining a high value of a medicinal agent adapted for treatment of germ diseases, boils, goiter, skin diseases and infections; to, provide a non-toxic germicide that will penetrate and which will not burn, stain or in any way irritate the skin.

I have found that when vegetable oils containing fatty acids are treated with a medicinal agent such as the elements of' the halogen group or compounds thereof, the medical agent combines with the fatty aclds of the oil forming saturated halogenated hydroxy fatty acids. These saturated hydroXy-f'atty acids are readily converted into sulphuric ester by the treatment with concentrated sulphuric acid forming a compound having a high degree of solubility in water, which successfully resists decomposition in very dilute solutions. The resulting compound is highly dlsmfectant and lts "germicidal properties render it well suited for treatment of germ diseases, boils, goiter, skin diseases and infections.

Numerous different oils, both vegetable and animal, containing fatty acids of many different varieties, may be used in the prep- 7 Application filed August 30, 1928. Serial No. 303,128.

from thirty minutes to one hour or until all albuminous matter is precipitated, coagulated and settled out. Then the ricinoleic acid istreated with a quantity of iodine substan tially equal to 10% by volume of the quantity of acid. The iodine may be introduced in the form ofa solution, in crystalline form or as hydriodic acid. The percentage of iodine may varydecideclly from 107% if desired, but in all events it is necessary that the quantity of iodine introduced be insufficient to saturate all of the ricinoleic acid with iodine' The iodized ricinoleic acid is then allowed to stand for five or six days before treatment withsulphuric acid.

The reaction between the ricinoleic acid and the iodine may be illustrated by the following equation:

t r can... (on (our zoozn The reaction product produced is ricinoleic acid, di-iodide, or diiodo-mono-hydroxystearic acid. Although all the ricinoleic acid is not saturated with iodine because of the insuflicient quantity introduced some of the ricinoleic acid takes on iodine to the extent of becoming completely saturated, and

theproduct at the end of the iodinization reaction is a saturated hydroxy-fatty acid.

The iodized ricinoleic acid is then treated with a quantity of chemically pure sulphuric acid substantially equal to 30% by volume of the product of the previous reaction at a temperature not higher than 30 C. Generally 8 hours are required to complete sodium salt.'

this step of the process. This reaction is illustrated by the following equation:

The reaction product is sulphuric ester of di-diodo hydroxy stearic acid. -This prod uct is then separated from the by-products of the reaction and completely neutralized by any suitable alakali such as sodium hydroxide producing the following sodium salt of the compound:

ownsowsosn onrpoozna.

This compound is sulphuric ester of 9-10 di-iodo7 hydroxy sodium'stearate, 9-1O referring to the positions of the iodine and 7 the position of the sulphuric acid group in thefatty acid chain.

The sodium salt of the compound is then separated from the impurities mixed therewith by dissolving the salt in a suitable solvent such as alcohol and centrifuging the solvent 01f.

The final product may be left in a dilute statein solution in alcohol; the solution may be'concentrated by driving off part'of the alcohol, or all of the alcohol may be driven off by distillation leaving the sodium salt of the compound in a plastic form.

Although'but one specific example of my invention'has been herein described, it will be understood that various changes in the details and sequence of steps of the process and substitutions of ingredients may be made without departing from the spirit of this invention as defined by the following claims:

r -I claim:

1 The method of preparing a pharmaceutical compound consisting of the addition of concentrated sulphuric acid to a hydroxy fatty acid havingan element of the halogen group combined therewith and formingan organic sulphate of the halogenated fatty acid.

2. The method of preparing a pharmaceutical composition consisting of saturating unsaturated hydroXy fatty acids with a halogen element, and adding concentrated sulphuric acid to the halogenated fatty acid thereafter, and forming an alkali metal salt of the resulting product. 7

3. The method of preparing a pharmaceutical compound consisting of halogenating an unsaturated hydroxy fatty acid, reacting the halogenated fatty acid with sulphuric acidthereafter, and treating the resulting product with sodiumhydroxide to form a 4c- The method of manufacturinga germicide consisting of saturating a hydroxy fatty acid of an oil with a halogen element and adding concentrated sulphuric acid thereafter, and treating the same with an the distillation of the alcohol therefrom. Signed at Chicago this 27th" day of August, 1928.

- WALTER T. WINCKLER. 

